The present invention relates to a novel pyrazole derivative, an insecticidal and miticidal composition containing the derivative as an active ingredient and a fungicidal composition containing the derivative as an active ingredient.
Examples of compounds having similar structures to that of the pyrazole derivative of the present invention include the compounds described in Pest. Bio. Phy., 25, 163 (1986) and Japanese Patent Laid-Open (KOKAI) Nos. 52-87168 (1977) and 60-34949 (1985) which each have fungicidal activity; the compound described in Japanese Patent Laid-Open (KOKAI) No. 57-106665 (1982) which has herbicidal activity and the compounds respectively described in Japanese Patent Laid-Open (KOKAI) Nos. 47-6269 (1972), 48-56671 (1973), 52-83840 (1977), 56-73071 (1981) and 59-95272 (1984), Japanese Patent Publication No. 55-44751 (1980) and J. Pharm. Sci., 74, 1013 (1985) which each have medicinal activity. However, there is no description with respect to insecticidal and miticidal activities. None of the above-described publications and literature also describes an aralkyl group as a substituent for the amide moiety of the compound.
On the other hand, Farmaco. Ed. Sci., 22, 692 (1967) describes N-benzyl-3-methyl-5-pyrazolecarboxamide and benzyl 3-methyl-5-pyrazolecarboxylate, Rev. Roum. Chim., 23, 1581 (1978) describes N-benzyl-1-(2,4-dinitrophenyl)-3-biphenyl-5-pyrazolecarboxamide, and Japanese Patent Laid-Open (KOKAI) No. 50-58056 describes N-(4-hydroxybenzyl)-1,3-dimethyl-5-pyrazolecarboxamide and N-(4-hydroxycarbonylmethoxybenzyl)1,3-dimethyl-5-pyrazolecarboxamide. However, none of these reports describes the presence of insecticidal, miticidal and fungicidal activities of the compounds disclosed therein.
Although it has been described in Japanese Patent Laid-Open (KOKAI) Nos. 63-246367 (1988) and 63-135364 (1988) that N-(.alpha.-cyanobenzyl)-5-pyrazolecarboxamides have fungicidal activity, the compound disclosed therein is characterized by the cyano group on the .alpha.-position of the benzyl group. In Japanese Patent Laid-Open (KOKAI) No. 63-91373 (1988), N-(alkyl, substituted or non-substituted phenyl or benzyl)-1-(substituted or non-substituted phenyl)-5-pyrazolecarboxamide has been proposed as a plant growth regulator or a toxicity mitigator.
Japanese Patent Laid-Open (KOKAI) No. 62-120369 (1987) discloses N-(substituted or non-substituted benzyl)-1-(substituted phenyl)-4-(nitro or cyano)-5-pyrazolecarboxamides. The compound disclosed therein is characterized to have a nitro group or a cyano group as the substituent on the 4-position of the pyrazole ring, however, any examples of N-(substituted or non-substituted benzyl)-5-pyrazolecarboxamide have not been described therein.
Japanese Patent Laid-Open (KOKAI) No. 63-258859 (1988) discloses N-(substituted or non-substituted aralkyl)-1-(substituted phenyl)-4-(substituted thio, substituted sulfoxy or substituted sulfonyl)-5-pyrazolecarboxamides. Although these compounds are characterized by having a substituted thio group, a substituted sulfoxy group or a substituted sulfonyl group as the substituent on the 4-position, any examples of N-(substituted or non-substituted aralkyl)-5-pyrazolecarboxamides have not been described therein.
Synthesis, 727 (1981); Farmaco, Ed.Sci., 38, 369 (1983) and J. Med.Chem., 27, 986 (1984) disclose that N-(substituted or non-substituted benzyl)-3-methyl-4-nitro-5-pyrazolecarboxamide has medicinal activity.
Japanese Patent Publication (KOKOKU) No. 48-15300 (1973) discloses that N-(dibenzyl or dialkyl)-3-methyl-5-pyrazolecarboxamide has medicinal activity.
Although Japanese Patent Application No. 63-53165 (1988) and Japanese Patent Application No. 63-175450 (1988) disclose compounds having similar structures to those of the compounds of the present invention, only aralkyl such as benzyl and naphthylmethyl which may have substituents are disclosed as a substituent for the amide moiety.
The examples in which the substituent for the amide moiety is aralkyl have been described in detail as above.
As the compound in which the substituent for the amide moiety contains a hetero ring, N-(2-chloro-3-pyridyl)-1,3-dimethyl-4-nitro-5-pyrazolecarboxamide (Ger. Offen. DE 3,122,670) and N-pyridyl-3-methyl-5-pyrazolecarboxamide (Japanese Patent Laid-Open (KOKAI) No. 54-9278 (1979) are mentioned. In these compounds, the substituent for the amide moiety is a pyridyl group, and there is no description about insecticidal activity, miticidal activity and fungicidal activity of the compounds.
Japanese Patent Laid-Open (KOKAI) Nos. 63-246367 (1988) and 63-119463 (1988) disclose that the compound in which the substituent for the amide moiety is a hetero ring substituted methyl group, such as N-(.alpha.-cyanothienylmethyl)-1,3-dimethyl-5-pyrazolecarboxamide, shows fungicidal activity. However, any of the hetero ring substituted methyl groups in the compound disclosed therein has a cyano group at .alpha.-position thereof and a pyridylmethyl group is not disclosed therein as the hetero ring substituted methyl group.
The compounds disclosed in the prior publication have been given above in detail, however, the compound in which the acid moiety is a pyrazole and the substituent for the amide moiety is a pyridylmethyl group has not been reported.
Since harmful insects have recently had resistance to insecticides due to use of insecticides for many years, it has been difficult to control insects by conventional insecticides. For example, insect having resistance to organophosphorous compounds and carbamate compounds which are both typical insecticides have been widely generated, resulting in the difficulty of control of these insects. In addition, the presence of insects having the resistance to synthetic pyrethloid-type insecticides which have recently attracted attention has been reported. On the other hand, some of the organophosphorous compounds or carbamate compounds exhibit high toxicity, and some of them disturb the ecological system due to their high residual effect to bring about an extremely anxious problem. Therefore, it is expected to develop a novel insecticide which exhibits an excellent controlling effect even against insects and mites having resistance to conventional insecticides and which has low toxicity and low residual effect.
The controlling effect of fungicides for agricultural and horticultural use has been reduced also by the generation of fungus which has gained resistance to the conventional fungicides, and accordingly, the development of a novel fungicide has been expected.
As a result of the investigations performed by the present inventors for solving such a problem, a novel pyrazole derivative which has excellent insecticidal, miticidal and fungicidal activities has been found.
The present invention has been accomplished based on this finding.